The conformation of histamine in solution: 1H nuclear magnetic resonance study

Casy, A. F.; Ison, R. R.; Ham, Norman S.

doi:10.1039/c29700001343

Cited by 18 publications

(8 citation statements)

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“…The molecule, corresponding to that suggested by Kier, would be an indirectly acting phenethylamine. Several authors, inter alia Kier (1968c), Kier & Truitt (1970), Chothia & Pauling (1969), Bergin (1971a) and Pullman et al (1972) have calculated various intra molecular distances in order to ascertain the essential features of a sympathomimetic molecule. The distances considered to be of interest involve primarily the charged nitrogen atom in respect to different hydroxyl groups and also the height of the nitrogen atom above the ring plane.…”

Section: B Conformational Aspects On Phenethylaminesmentioning

confidence: 99%

Molecular characteristics of biogenic monoamines and their analogs

Carlström

Bergin

Falkenberg

1973

Quart. Rev. Biophys.

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Until recently there has been very limited information concerning the molecular geometry and conformation of biogenic monoamines and this lack of knowledge has seriously hampered efforts to unravel the structure—function relationships at the molecular level. Nevertheless, several theories have been proposed regarding interaction between the monoamines and their receptor sites. This is especially true for the neurohumoral transmitters dopamine, noradrenaline (norepinephrine) and serotonin (5-hydroxytryptamine), the target areas of which seem to be specific not only in the sense of chemical structure but also from the steric point of view. The well-known differences in biological activity due to chiralty illustrate the importance of the three-dimensional architecture of the molecules and indicate also the presence of stereospecific receptor sites. A detailed knowledge of the conformation of the biogenic monoamines would not only elucidate the requirements upon a natural or synthetic monoamine for proper function but also give indirect information about the geometry of the receptor sites.

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Section: B Conformational Aspects On Phenethylaminesmentioning

confidence: 99%

Molecular characteristics of biogenic monoamines and their analogs

Carlström

Bergin

Falkenberg

1973

Quart. Rev. Biophys.

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“…The NMR solution studies on histamine [7,23,24] predict equal populations for the trans and gauche forms in the monocation, and a slight excess of trans form in the dication. Our results are in agreement with these data.…”

Section: Discussionmentioning

confidence: 98%

Calculation of the minimum energy conformation of biomolecules using a global optimization technique. IV. Preferred conformations and receptor maps of histamine

Rao

Mahajan

Mishra

2009

Int. J. Quantum Chem.

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The minimum energy conformations of the three cations of histamine that are present at physiologic pH have been calculated by the global optimization method of Subba Rao, Tyagi, and Mishra [J. Theor. Biol. 90, 377, 391 (1981)l. All three dihedral angles are varied. The classical potential function consisting of the electrostatic, nonbonded, and torsional terms is used. The results are in good agreement with those of other workers and with experimental data.

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“…16 In contrast to the crystalline phase, the structure of histamineH + in solution is more flexible and less well defined. NMR studies in aqueous solution 5,17 confirm that histamine occurs at pH E 7.4 with >96% as an ammonium monocation of both the Np and Nt tautomers, with the Nt form being slightly preferred and regarded as the physiologically active species when interacting, e.g., with the H 1 receptor. 5,9 However, at 37 1C the reported differences in free energy are less than 4 kJ mol…”

Section: Introductionmentioning

confidence: 98%

“…5,9,17,18 As already mentioned, the stabilization induced by solvation of the ammonium group in aqueous solution overrides the effects of intramolecular H-bonding to the imidazolium ion. This observation implies that during the ESI process, the proton is transferred from Na to Np.…”

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confidence: 99%